Azo compounds having a 5-substituted-4-chlorothiazolyl-2-diazo component radical

ABSTRACT

Compounds of the formula ##STR1## in which K is the radical of a coupling component of the aniline, α-naphthylamine, pyrazolone, aminopyrazole, indole, tetrahydroquinoline, thiazole, phenol, naphthol, pyridine or pyridone series. 
     R is --CHO, --CH═C(CN)--R 1 , --CH═CH--R 2 , --CH═C(NO 2 )--R 3 , --CH═NOH or --CN, 
     wherein R 1  is (C 1-10  alkoxycarbonyl; (C 1-10  alkoxy)carbonyl monosubstituted by chloro, bromo, cyano, hydroxy, C 1-2  alkoxy, (C 1-2  alkyl)carbonyloxy or (C 1-2  alkoxy)carbonyl; (C 1-10  alkoxy)carbonyl disubstituted by hydroxy and by chloro or bromo; (C 3-8  alkenyl)oxycarbonyl; (C 3-8  chloroalkenyl)oxycarbonyl; (C 3-8  bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl; chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C 1-4  alkylsulfonyl; phenylsulfonyl; tolylsulfonyl; carbamoyl; (C 1-2  alkyl)carbamoyl; di(C 1-2  alkyl)carbamoyl; phenylcarbamoyl; aminothiocarbonyl; benzimidazolyl-2; cyano; acetyl; phenyl; benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and 
     R 2  is phenyl; benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and 
     R 3  is hydrogen, methyl or ethyl, and 
     m is 0 or 1, useful as disperse dyes for dyeing and printing textile substrates comprising or consisting of synthetic or semi-synthetic, hydrophobic, high molecular weight, organic materials such as linear aromatic polyesters, cellulose 21/2 acetate, cellulose triacetate and synthetic polyamides, with those wherein R is formyl also being useful for dyeing wool.

The present invention relates to substituted 4-chlorothiazolylgroup-containing compounds, their production and use as dyestuffs.

More particularly, the present invention provides disperse dyestuffs offormula I, ##STR2## in which K is the radical of a coupling component ofthe aniline, α-naphthylamine, pyrazolone, aminopyrazole, indole,tetrahydroquinoline, thiazole, phenol, naphthol, pyridine or pyridoneseries,

R is --CHO, --CH═C(CN)--R₁, --CN, --CH═CH--R₂, --CH═NOH or--CH═C(R₃)NO₂,

R₁ is C₁₋₁₀ alkoxycarbonyl optionally monosubstituted by chlorine,bromine, cyano, hydroxyl, C₁₋₂ alkoxy, C₁₋₂ -alkylcarbonyloxy or C₁₋₂alkoxycarbonyl; C₁₋₁₀ alkoxycarbonyl disubstituted by a hydroxy groupand a chlorine or bromine atom; C₃₋₈ alkenyloxycarbonyl; chloro- orbromo-(C₃₋₈ -alkenyl)oxycarbonyl; propynyloxycarbonyl; benzyl-,chlorobenzyl- or nitrobenzyloxycarbonyl; C₁₋₄ alkylsulphonyl; phenyl orbenzyl optionally substituted by a total of up to three substituentsselected from chlorine, bromine and nitro (max. 2 nitro groups);phenylsulphonyl; tolylsulphonyl; aminocarbonyl; mono- or di(C₁₋₂alkyl)aminocarbonyl; phenylaminocarbonyl; aminothiocarbonyl;benzimidazolyl-2; cyano; or acetyl;

R₂ is phenyl or benzoyl optionally substituted by a total of up to threesubstituents selected from chlorine, bromine and nitro (max. 2 nitrogroups);

R₃ is hydrogen, methyl or ethyl,

and m

is 0 or 1.

Preferred compounds of formula I are those in which the couplingcomponent is of the aniline, pyrazole or tetrahydroquinoline series,especially the aniline series.

Preferably K is K' where K' is a radical of formula ##STR3## in which R₅is hydrogen; C₁₋₂ alkyl; C₁₋₂ alkoxy; cyano; formylamino;alkylcarbonylamino in which the alkyl moiety is optionallymonosubstituted by hydroxyl, chlorine, bromine, alkoxy, phenyl, phenoxy,benzyloxy or (C₁₋₂ alkoxy)carbonyl; benzoylamino; acryloylamino;allylcarbonylamino; aminocarbonylamino; alkylaminocarbonylamino;alkoxycarbonylamino in which the alkoxy moiety is optionallymonosubstituted by C₁₋₂ alkoxy or phenyl; C₁₋₂ alkyl- orphenylsulphonylamino; di-C₁₋₂ alkylaminosulphonylamino; chlorine orbromine;

R₆ is hydrogen, chlorine, bromine, C₁₋₂ -alkyl, C₁₋₂ alkoxy, C₁₋₂alkoxyethoxy, with the proviso that only one of R₅ and R₆ can signifychlorine or bromine;

either

R₇ is hydrogen; C₁₋₈ alkyl; C₁₋₄ alkyl substituted by up to twosubstituents selected from chlorine, bromine, hydroxyl, thiocyano,cyano, alkylcarbonyl, alkoxycarbonyl, formyloxy, (C₁₋₁₀alkyl)carbonyloxy, cyclonexyl, chloro- or bromo-(C₁₋₃ alkyl)carbonyloxy,(C₁₋₁₀ alkoxy)carbonyloxy, C₁₋₂ alkoxyethoxycarbonyloxy,alkenyloxycarbonyl, chloro- or bromoallyloxycarbonyl, alkenyloxy,chloro- or bromoallyloxy, propynyloxy, benzoyloxy, alkoxy, phenyl,phenoxy and phenylalkoxy, with the proviso that such substituted alkylbears no more than one aryl-containing group; alkoxyalkyl in which thealkoxy moiety is monosubstituted by chlorine, bromine, cyano, alkoxy,alkoxycarbonyl, alkoxycarbonyloxy or alkylcarbonyloxy; β-alkyl-; alkenyloptionally monosubstituted by phenyl, chlorine or bromine; propynyl;C₅₋₇ cycloalkyl; cyclohexyl substituted by one, two or three methylgroups; phenyl optionally substituted by a total of up to threesubstituents selected from chlorine, bromine, methyl and C₁₋₂ alkoxy,

or

R₇ together with R₈ forms a piperidine or morpholine ring,

R₈ is hydrogen; C₁₋₈ alkyl; C₁₋₄ alkyl, monosubstituted by chlorine,bromine, hydroxyl, cyano, thiocyano, alkylcarbonyl, alkoxycarbonyl,formyloxy, alkylcarbonyloxy, chloro- or bromoalkylcarbonyloxy,alkoxycarbonyloxy, C₁₋₂ alkoxyethoxycarbonyloxy, alkenyloxycarbonyl,chloro- or bromoallyloxycarbonyl, alkenyloxy, chloro- or bromoallyloxy,propynyloxy, benzyloxy, alkoxy, phenyl, phenoxy, phenylalkoxy,aminocarbonyl, alkyl- or dialkylaminocarbonyl, alkyl- ordialkylaminocarbonyloxy, phenylaminocarbonyl, phenylaminocarbonyloxy,phthalimidyl-2, succinimidyl-2, saccharinyl-2, pyridyl orbenzothiazolyl-2-mercapto; alkoxyalkyl in which the alkoxy moiety ismonosubstituted by chlorine, bromine, cyano, alkoxy, alkoxycarbonyl,alkoxycarbonyloxy or alkylcarbonyloxy; β-hydroxy-, β-alkylcarbonyloxy orβ-alkenylcarbonyloxy-γ-allyloxy or γ-propynyloxypropyl; alkenyloptionally monosubstituted by chlorine, bromine or phenyl or,

R₈ together with R₇ form a heterocyclic ring as given above,

any alkyl and alkoxy radicals or moieties, unless otherwise specified,contain 1 to 4 carbon atoms and any alkenyl radicals or moieties contain3 or 4 carbon atoms , or K' is the radical of a coupling component ofthe pyrazole or tetrahydroquinoline series.

More preferably K is K", where K" is a coupling component radical offormula VI ##STR4## in which R_(x) is hydroxyethyl, methyl, ethyl,methoxycarbonylethyl, ethoxycarbonylethyl, benzyl, methoxyethyl,ethoxyethyl or acetoxyethyl, and

R_(y) is hydrogen, methyl or acetylamino,

or a radical of formula II.

Even more preferably K is K"', where K"' is a radical of formula II.

R₅ is preferably R₅ ', where R₅ ' is hydrogen, methyl or --NHCOR₉, whereR₉ is hydrogen, C₁₋₄ alkoxy, C₁₋₂ -alkoxyethoxy or C₁₋₂ alkyl optionallymonosubstituted by chlorine, bromine or C₁₋₂ alkoxy.

Most preferably R₅ is hydrogen or methyl.

R₆ is preferably R₆ ', where R₆ ' is hydrogen, methyl, methoxy, ethoxyor C₁₋₂ alkoxyethoxy.

Most preferably R₆ is hydrogen.

Preferably R₇ and R₈ have a significance other than forming aheterocyclic ring.

Among the preferred significances of R₇, when it is a disubstitutedalkyl group, are β-hydroxy or (C₁₋₄ alkyl)carbonyloxy-γ-allyloxy orpropynyloxy-propyl.

R₇ is preferably R₇ ', where R₇ ' is hydrogen, C₃₋₄ alkenyl, C₁₋₆ alkylor C₂₋₃ alkyl monosubstituted by hydroxy, allyloxy, propynyloxy, cyano,(C₁₋₄ -alkoxy)carbonyl or (C₃₋₄ alkenyl)oxycarbonyl or substituted by upto two substituents selected from C₁₋₃ alkoxy, (C₂₋₃ alkyl)carbonyloxyand (C₁₋₃ alkoxy)carbonyloxy.

Most preferably R₇ is (C₁₋₄)alkyl

R₈ is preferably R₈ ', where R₈ ' is C₁₋₄ alkyl, benzyl, phenylethyl orC₂₋₃ alkyl monosubstituted by hydroxy, C₁₋₃ alkoxy, allyloxy,propynyloxy, cyano, (C₁₋₃ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyl,(C₃₋₄ alkenyl) oxycarbonyl, (C₂₋₃ alkoxy)carbonyloxy or phenoxy.

Most preferably R₈ is (C₁₋₄ alkyl).

Most preferably K is K^(iv), where K^(iv) is a radical of formula IIwherein R₅ is R₅ ', R₆ is R₆ ', R₇ is R₇ ' and R₈ is R₈ '.

It will be appreciated that the substituents are chosen such that themolecule is free from groupings such as ##STR5##

R₁ is preferably R₁ ', where R₁ ' is (C₃₋₆ alkoxy) carbonyl or (C₃₋₆alkenyl)oxycarbonyl.

Any phenyl or benzoyl as R₂ which is substituted is preferablymonosubstituted.

R₃ is preferably hydrogen.

m is preferably 0.

R is preferably R', where R' is --CHO, --CH═C(CN)R₁ or --CH═CR₃ --NO₂.

More preferably R is R", where R" is --CHO, --CH═C(CN)R₁ ' or--CH═CHNO₂.

Most preferably R is R"', where R"' is --CHO or --CH═C(CN)--R₁ '.

Preferred compounds of formula I are

(1) those wherein K is K', more preferably K";

(2) those wherein K is K"', especially those wherein R is R' morepreferably R";

(3) those wherein K is K^(iv) and R is R";

(4) those of (1), (2) or (3) wherein m is 0;

(5) those of (2), (3) or (4) wherein R is R'";

(6) those of (3) wherein R₅ is hydrogen or methyl,

R₆ is hydrogen, R₇ and R₈ are both ethyl, m is 0 and R is R"'.

The present invention further provides a process for the production of acompound of formula I, comprising coupling a diazotized amine of formulaIII, ##STR6## with a compound of formula IV,

    H--K                                                       (IV)

Diazotization and coupling are carried out in accordance with knownmethods. Compounds of formula I in which R is formyl may be converted toother compounds of formula I by reacting the formyl compounds with thecorresponding active methylene compound.

The compounds of formula III wherein R is formyl may be prepared byreacting the compound of formula V ##STR7## or a salt thereof, with aVilsmeier reagent, e.g. the reaction product of phosphorus oxychlorideand dimethylformamide, and the resulting product of formula IIIa##STR8## is hydrolysed to the 2-amino compound by heating in an acid orbasic medium.

The compounds of formula III wherein m is 1 may be formed by reactingcompounds of formula V with vinylic Vilsmeier reagents, followed byhydrolysis. Vinylic Vilsmeier reagents may be obtained, for example, byreacting phosphorus-oxychloride with (CH₃)₂ --NCH═CH--CHO.

Further, the compounds of formula I or III wherein R is formyl may beconverted into other compounds of Formula I or III by known methods, forexample condensation with hydroxylamine and optionally acylating theoxygen with nitrile formation; preparation of Schiff's bases,Knoevenagel, Perkin or Wittig-Horner reactions; aldol additions etc.

The disperse dyestuffs of formula I may be used for dyeing or printing,from aqueous dispersion, textile substrates consisting of or comprisingsynthetic or semi-synthetic, hydrophobic, high molecular weight organicmaterials. Preferred textile substrates are those which consist of orcomprise linear, aromatic polyesters, cellulose 21/2 acetate, cellulosetriacetate and synthetic polyamides.

The compounds of formula I may be made up into dyeing preparations inknown manner by grinding in the presence of dispersing agents and/orfillers optionally with vacuum or spray drying. After the addition ofwater the preparations may be used in the so-called long or shortdyebaths. Dyeing and printing may be carried out in accordance withknown methods.

The dyeings obtained have notable light-, thermofixation-, sublimation-and pleating-fastness.

The compounds of formula I wherein R is formyl are also useful fordyeing wool.

The following Examples further serve to illustrate the invention. In theExamples all parts are by weight and all temperatures are in degreesCentigrade.

EXAMPLE 1

To 73 parts N,N-dimethylformamide at 0° to 5° are added dropwise, 46parts phosphorus-oxychloride. 15.2 parts2-aminothiazolin-4-one-hydrochloride are added portionwise at 0° to 5°to the colourless solution of the Vilsmeier complex. The cooling bath isremoved and the mixture is heated to 70°. After 14 hours stirring thesolution is allowed to cool and is added carefully to a mixture of 41parts sodium acetate, 60 parts water and 50 parts ice. The brown-redsolution is stirred at 50° for 2 hours whereby the2-amino-4-chloro-5-formylthiazole formed by hydrolysis precipitatessuccessively. The yellow product is filtered after cooling to roomtemperature.

16.25 Parts product are added without further purification in smallportions to a mixture of nitrosylsulphuric acid (obtained by heating asolution of 6.9 parts sodium nitrite in 140 parts sulphuric acid at 70°)in 100 parts phosphoric acid cooled to 0°. The mixture is stirred for 1hour whilst being maintained at 0°. The resulting diazonium saltsolution is added over a period of 30 minutes to a mixture of 32.2 parts3-[N-cyanoethyl-N-(γ-chloroallyl)-amino]-4-ethoxyacetanilide, 5 partsamidosulphonic acid and 500 parts 5% aqueous sulphuric acid. Thedyestuff suspension is stirred for 1 hour at 0°, filtered, washed freeof acid and salt and dried.

The dyestuff obtained, of formula ##STR9## dyes linear, aromaticpolyester or cellulose acetate in brilliant blue shades with goodfastness.

In the following Table further dyestuffs which are made in analogy withthe procedure given above are given. They correspond to the generalformula ##STR10##

    TABLE 1            Shade on Ex.      polyester No. R R.sub.6 R.sub.5 R.sub.7 R.sub.8     fibres      2 CHO OC.sub.2 H.sub.5 NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5     blue 3 " " NHCOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCOC.sub.2 H.sub.5     CH.sub.2 CH.sub.2 OCOC.sub.2 H.sub.5 " 4 " " NHCOCH.sub.3 CH.sub.2     CH.sub.2 OCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5 " 5 " O     CH.sub.3 " CH.sub.2 CH.sub.2 OCOCH.sub.3 CH.sub.2 CH.sub.2 OCOCH.sub.3 "     6 " " NHCOOCH.sub.3 CH.sub.2 CH.sub.2 OCH hd 3 CH.sub.2 CH.sub.2     OCH.sub.3 " 7 " " NHCOCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CHCH.sub.2     CH.sub.2 CH.sub.2 OCH.sub.2 CHCH.sub.2 " 8 " " " CH.sub.2 CH.sub.2     OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5 "     9 " OC.sub.2 H.sub.5 NHCOCH.sub.2 Cl CH.sub.2 CH.sub.2 OCH.sub.2 CCH     CH.sub.2 CH.sub.2 OCH.sub.2 CCH " 10 " " NHCOCH.sub.2 CH.sub.2 OCH.sub.3 C     .sub.2 H.sub.5 C.sub.2 H.sub.5 " 11 " OCH.sub.3 NHSO.sub.2 CH.sub.3     n-C.sub.4 H.sub.9 n-C.sub.4 H.sub.9 " 12 " " NHCOCH.sub.3 CH.sub.2     CHCHCl CH.sub.2 CHCHCl " 13 " " NHCONH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2     CHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2      CHCH.sub.2 " 14 " " NHCOCHClCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 "     15 " " NHCOOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 " " "  16 " " CH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2     CHCH.sub.2 " 17 " " " n-C.sub.4 H.sub.9 NC.sub.4 H.sub.9 " 18 " " "     CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OH " 19 " " "     CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 "     20 " " "      C.sub.2 H.sub.5 "  21 " " " CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 "     22 " OC.sub.2 H.sub.5 NHCOCH.sub.3 " " " 23 " OCH.sub.3CH.sub.3 CH.sub.2     CHCHCl CH.sub.2 CHCHCl " 24 " " "  CH.sub.2 CH.sub.2 COOCH.sub.2 CHCHCl     H violet 25 " H NHCOCH.sub.3 CH.sub.2 CH.sub.2 CN CH.sub.2 CH.sub.2     OCOCH.sub.3 " 26 " H NHCOCHOHCH.sub.3 n-C.sub.4 H.sub.9 n-C.sub.4     H.sub.9 " 27 " H NHCOOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 C.sub.2 H.sub.5 C     .sub.2 H.sub.4 OH " 28 " H NHCOC.sub.2 H.sub.4 Cl " C.sub.2 H.sub.5 " 29     " H NHCOC.sub.6 H.sub.5 CH.sub.3 H " 30 " H CH.sub.3 C.sub.2 H.sub.5     CH.sub.2 CH.sub.2 OCONHC.sub.6 H.sub.5 " 31 CHNOH H " CH.sub.2 CH.sub.2     OCH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CHCH.sub.2 ruby 32 " H     H CH.sub.2 CH.sub.2 CN C.sub.2 H.sub.5 " 33 " H H CH.sub.2 CH.sub.2 CN     CH.sub.2 CH.sub.2 OCOCH.sub.3 " 34 " H H CH.sub.2 CH.sub.2 OCOCH.sub.3 "     " 35 " H H CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 CN " 36 " H H CH.sub.2     CH.sub.2 OCOOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 " " 37 CN H H CH.sub.2     CH.sub.2 OCH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 red 38 "     H H CH.sub.2 CH.sub.2 CN CH.sub.2 CH.sub.2 CN " 39 " OC.sub.2 H.sub.5     NHCOCH.sub.3 CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 blue 40 " OCH.sub.3     " CH.sub.2 CH.sub.2 CN CH.sub.2 CHCH.sub.2 " 41 CHO OC.sub.2 H.sub.5 "     C.sub.2 H.sub.4 COOCH.sub.3 H " 42 " OCH.sub.3 " C.sub.2 H.sub.4     COOC.sub.2 H.sub.5 H " 43 " " " C.sub.2 H.sub. 4 COO(CH.sub.2).sub.3     CH.sub.3 H " 44 " " " C.sub.2 H.sub.4 COOCH.sub.2 CHCHCl H " 45 "     OC.sub.2 H.sub.5 " C.sub.2 H.sub.4 COOCH.sub.2 CHCH.sub.2 H "  46 " " "      ##STR11##      H "  47 " " " CH(CH.sub.3)(CH.sub.2).sub.3 CH.sub.3 H " 48 " " "     CH(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5 H " 49 " " " C.sub.2 H.sub.4     OCOCH.sub.3 H " 50 " OCH.sub.3 " C.sub.2 H.sub.4 OCOCH.sub.3 CH.sub.2     CHCH.sub.2 " 51 " " " C.sub.2 H.sub.4 CN H " 52 " OCH.sub.3 " " CH.sub.2     CHCHCl " 53 " OC.sub.2 H.sub.5 " CH.sub.3 H " 54 " OC.sub.2 H.sub.5 "     CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.4 COOCH.sub.3 " 55 " " " CH.sub.2     CHCHCl " " 56 " " " C.sub.2 H.sub.4 OCOCH.sub.3 " " 57 " " " CH.sub.2     CHOHCH.sub.3 " " 58 " " " C.sub.2 H.sub.4 COOCH.sub.3 " " 59 " " "     CH.sub.2 CCH C.sub.2 H.sub.4 COOC.sub.2 H.sub.5 " 60 " " " CH.sub.2     CHOHCH.sub.2 Cl " " 61 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5     violet 62 " H " " C.sub.2 H.sub.4 OCH.sub.2 CHCH.sub.2 " 63 " H " "     C.sub.2 H.sub.4 OH " 64 " H " " C.sub.2 H.sub.4 OCOCH.sub.3 " 65 " H " "     CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 OCOCH.sub.3 " 66 " H " " CH.sub.2     CHOHCH.sub.2 CH.sub.3 " 67 " H " " CH.sub.2 CHOHCH.sub.2 Cl " 68 " H " " C     H.sub.2CH.sub.2 OC.sub.6 H.sub.5 " 69 " H " " CH.sub.2 CHCH.sub.2 " 70 "     H " " CH.sub.2 CHCHCl " 71 " H " " CH.sub.2 C(CH.sub.3)CH.sub.2 " 72 " H     " " CH.sub.2 CHOHCH.sub.2 OCH.sub.2 CCH " 73 " H " " CH.sub.2C.sub.6     H.sub.5 " 74 " H " " C.sub.2 H.sub.4 OCOCH.sub.2 Cl " 75 " H " " C.sub.2     H.sub.4 CONHC.sub.6 H.sub.5 " 76 " H " " CH.sub.2 CH.sub.2 COOCH.sub.3 "     77 " H " " CH.sub.2 CHOHCH.sub.2 SCN " 78 " H " " CH.sub.2 CH.sub.2     OCONHCH.sub.3 " 79 " H " " CH.sub.2 CHOHCH.sub.3 "      80 " H " "     ##STR12##      "  81 " H NHCOCH.sub.3 " C.sub.2 H.sub.5 " 82 " H " " CH.sub.2 CH.sub.2     COOC.sub.2 H.sub.5 " 83 " H " CH.sub.3 CH.sub.2 C(CH.sub.3)CH.sub.2 " 84     " H " CH.sub.2 CH(CH.sub.3)CH.sub.3 CH.sub.2 CH(CH.sub.3)CH.sub.3 " 85 "     H NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 CH.sub.2 CH.sub.2     OCOCH.sub.3 " 86 " H NHCOC.sub.2 H.sub.4 Cl CH.sub.3 C.sub.2 H.sub.4     OCOOC.sub.2 H.sub.5 " 87 " H NHCOC.sub.2 H.sub.5 CH.sub.2 CHCH.sub.2     CH.sub.2 CH.sub.2 COOCH.sub.3 " 88 " H NHCOCH.sub.3 C.sub.2 H.sub.4 CN     CH.sub.2 CHCHCl " 89 " H NHCHO C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4     OCH.sub.3 " 90 " H NHCOOC.sub.2 H.sub.4 OC.sub.2 H.sub.5 CH.sub.2     CHCH.sub.2 CHCHCH.sub.2 " 91 " H Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 " 92     " H CN " n-C.sub.4 H.sub.9 " 93 " H H " CH.sub.2 CH(CH.sub.3)CH.sub.3 "     94 " H H n-C.sub.3 H.sub.7 n-C.sub.3 H.sub. 7 " 95 " H H n-C.sub.4     H.sub.9 n-C.sub.4 H.sub.9 " 96 " H H CH.sub.3 n-C.sub.6 H.sub.13 " 97 "     H H C.sub.2 H.sub.4 OH n-C.sub.8 H.sub.17 " 98 " H H C.sub.2 H.sub.4 CN     CH.sub.2 CBrCH.sub.2 ruby 99 " H H " CH.sub.2 CH.sub.2 OCOCH.sub.3 "     100      ##STR13##      blue

EXAMPLE 101

(a) A diazonium solution is prepared as described in Example 1 and isadded to a mixture of 16.3 parts 1-diethylamino-3-methylbenzene, 5 partsamidosulphonic acid and 100 parts 10% aqueous sulphuric acid. Thedyestuff obtained of formula (a) ##STR14## dyes textiles of linear,aromatic polyesters and cellulose acetate in brilliant violet shadeswith good fastnesses.

(b) 8.4 Parts of the dyestuff of formula (a) are suspended in 40 partsdioxane, 7 parts cyanoacetic-acid-n-butylester, 1 part glacial aceticacid and 1 part piperdine. Stirring is effected for 2 hours at 25° andthe condensation product of formula (b) ##STR15## is filtered off. Thedyestuff dyes textile materials of linear, aromatic polyesters orcellulose acetate in very brilliant blue shades with good lightfastness.

(c) The dye of (b) can also be obtained by the following reactionscheme. ##STR16##

Reaction step ○1 is described in Example 1.

Reaction step ○2

16.25 Parts 2-amino-4-chloro-5-formylthiazole are suspended in 100 partsethanol, 28 parts cyanoacetic acid-n-butylester, 1 part glacial aceticacid and 1 part piperidine and are stirred for 3 hours at 55° C. Thewhole is cooled to 0° and the condensation product of formula ##STR17##is filtered off and dried in a vacuum cupboard at 50°.

Reaction step ○3

28.5 Parts of the product of reaction step ○2 are dissolved in 150 parts85% phosphoric acid and added dropwise over 20 minutes at -5° to 34parts 40% nitrosylsulphuric acid. The mixture is stirred for 2 hours at-5°. The resulting diazonium salt solution is added over 30 minutes to amixture of 16.3 parts 1-diethylamino-3-methylbenzene, 5 partsamidosulphonic acid and 500 parts 10% aqueous sulphuric acid. The greyblack dyestuff suspension is stirred at 0° for 1 hour and then filteredoff from the mother liquor. The filter cake is washed acid free anddried in a vacuum cupboard at 50°.

The dyestuffs of the following Table 2 are made in analogous manner tothe procedure described in Examples 1 and 101. They correspond to theformula ##STR18## and dye polyester in blue shades with good fastnesses.R₅ is methyl in Examples 102 to 134 and 161 to 168, hydrogen in Examples135 to 160, methoxy in Examples 169 and 170, acetylamino in Examples 171to 177 and 181 to 199, propionylamino in Example 178,methoxycarbonylamino in Example 179, β-chloropropionylamino in Example180 and β-ethoxyethoxycarbonylamino in Example 200.

In Examples 102 to 160 and 171 to 180 R₆ is hydrogen, in Examples 161 to170 and 186 to 191 it is methoxy and in Examples 181 to 185 and 192 to200 it is ethoxy. In Examples 101 to 200 R is a group of formula (a)--COOCH₂ CH₂ CH₂ CH₃, (b) --COOCH₂ C(CH₃)═CH₂, (c) --COOCH₂ CH(CH₃)₂,(d) --COOCH₂ CH₂ CH₃, (e) --COOCH₂ CH₂ CH₂ Cl, (f) --COOCH₂ CH═CHCl, (g)--COOCH₂ CH₂ CH₂ CH₂ CH₃, (h) --COOCH(CH₃)₂ resp. (i) --COOCH₂ CH═CH₂.

                                      TABLE 2                                     __________________________________________________________________________    Ex.                                                                           No.                                                                              R.sub.7          R.sub.8                                                   __________________________________________________________________________    102                                                                              C.sub.2 H.sub.5  CH.sub.2 CH.sub.2 CH.sub.3                                103                                                                              "                CH.sub.2 CH.sub.2 OCOCH.sub.3                             104                                                                              "                CH.sub.2 CHOHCH.sub.3                                     105                                                                              "                CH.sub.2 CHOHCH.sub.2 CH.sub.3                            106                                                                              "                CH.sub.2 CH(OCOCH.sub.3)CH.sub.3                          107                                                                              "                CH.sub.2 CHCH.sub.2                                       108                                                                              "                CH.sub.2 C(CH.sub.3)CH.sub.2                              109                                                                              "                CH.sub.2 CHCHCl                                           110                                                                              "                CH.sub.2 CHOHCH.sub.2 CL                                  111                                                                              "                CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                        112                                                                              "                CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 OCOCH.sub.3              113                                                                              "                CH.sub.2 CH.sub.2 OCH.sub.3                               114                                                                              "                CH.sub.2 CHOHCH.sub.2 OCH.sub.2 CCH                       115                                                                              "                CH.sub.3                                                  116                                                                              "                CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                      117                                                                              "                CH.sub.2 CH.sub.2 OCH.sub.2CHCH.sub.2                     118                                                                              "                 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                      119                                                                              "                CH.sub.2 CH.sub.2OCH.sub.2 CCH                            120                                                                              "                CH.sub.2 CH.sub.2 OCOOC.sub.2 H.sub.5                     121                                                                              "                C.sub.2 H.sub.4 CN                                        122                                                                              "                CH.sub.2 CH(CH.sub.3)CH.sub.3                             123                                                                              "                CH.sub.2 CH.sub.2 Cl                                      124                                                                              "                CH(CH.sub.3).sub.2                                        125                                                                              "                CH.sub.2C.sub.6 H.sub.5                                   126                                                                              CH.sub.3         CH.sub.3                                                  127                                                                              "                C.sub.2 H.sub.5                                           128                                                                              "                CH.sub.2 CH.sub.2 CH.sub.3                                129                                                                              "                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       130                                                                              "                CHCH.sub.2 OCOCH.sub.3                                    131                                                                              "                CH CHOHCH.sub.2 CH.sub.3                                  132                                                                              "                CH.sub.2 CH.sub.2 OCH.sub.3                               133                                                                              CH.sub.2 CHCH.sub.2                                                                            CH.sub.2 CHCH.sub.2                                       134                                                                              CH.sub.2 C(CH.sub.3)CH.sub.2                                                                   CH.sub.2 C(CH.sub.3)CH.sub.2                              135                                                                              CH.sub.2 CH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.2 CH.sub.3                                136                                                                              "                 CH(CH.sub.3).sub.2                                       137                                                                              CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       138                                                                              "                CH.sub.3                                                  139                                                                              C.sub.2 H.sub.5  CH.sub.2 CHOHCH.sub.2 CH.sub.3                            140                                                                              "                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       141                                                                              "                C.sub.2 H.sub.5                                           142                                                                              "                CH.sub.2 CH.sub.2 CH.sub.3                                143                                                                              "                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       144                                                                              "                CH.sub.2 CHCH.sub.2                                       145                                                                              "                CH.sub.2 C(CH.sub.3)CH.sub.2                              146                                                                              "                CH(CH.sub.3).sub.2                                        147                                                                              "                CH.sub.2 CH(CH.sub.3).sub.2                               148                                                                              "                CH.sub.2 CH(OCOCH.sub.3)CH.sub.3                          149                                                                              "                CH.sub.2 CHOHCH.sub.2 CH.sub.3                            150                                                                              CH.sub.3         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       151                                                                              "                CH.sub.2 CHOHCH.sub.2 CH.sub.3                            152                                                                              CH.sub.2 CH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.2 CH.sub.3                                153                                                                              "                CH.sub.2 CHCH.sub.2                                       154                                                                              CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       155                                                                              CH(CH.sub.3).sub.2                                                                             CH(CH.sub.3).sub.2                                        156                                                                              CH.sub.2 CH(CH.sub.3).sub.2                                                                    CH.sub.2 CH(CH.sub.3).sub.2                               157                                                                              CH.sub.2 C(CH.sub.3)CH.sub.2                                                                   CH.sub.2 C(CH.sub.3)CH.sub.2                              158                                                                              C.sub.2 H.sub.5  CH.sub.2 CH.sub.2 CH.sub.2 OCOCH.sub.3                    159                                                                              "                CH.sub.2 C.sub.6 H.sub.5                                  160                                                                              "                CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                      161                                                                              CH.sub.3         CH.sub.2 CH.sub.2 COOCH.sub.3                             162                                                                              "                CH.sub.2 CHOHCH.sub.2 CH.sub.3                            163                                                                              "                CH.sub.2 CHCHCl                                           164                                                                              C.sub.2 H.sub.5  CH.sub.2 CH.sub.2 CN                                      165                                                                              CH.sub.2 CHCH.sub.2                                                                            CH.sub.2 CHCH.sub.2                                       166                                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                                    CH.sub.2 CH.sub.2 OCH.sub.3                               167                                                                              H                CH.sub.2 CH.sub.2 COOCH.sub.2 CHCHCl                      168                                                                              "                CH.sub.2 CHOHCH.sub.2 Cl                                  169                                                                              "                CH.sub.2 CH.sub.2 COOCH.sub.2 CH(CH.sub.3).sub.2          170                                                                               CH.sub.3        CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                      171                                                                              "                C.sub.2 H.sub.5                                           172                                                                              "                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       173                                                                              C.sub.2 H.sub.5  C.sub.2 H.sub.5                                           174                                                                              "                CH.sub.2 CH.sub.2 COOCH.sub.3                             175                                                                              "                CH.sub.2 CHOHCH.sub.3                                     176                                                                              CH.sub.2CHCH.sub.2                                                                             CH.sub.2 CHCH.sub.2                                       177                                                                              CH.sub.2 CH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.2 CH.sub.3                                178                                                                              C.sub.2 H.sub.5  C.sub.2 H.sub.5                                           179                                                                              "                "                                                         180                                                                              "                "                                                         181                                                                              CH.sub.3         CH.sub.3                                                  182                                                                              "                CH.sub.2 CH.sub.2 OCOCH.sub.3                             183                                                                              "                CH.sub.2 CHCH.sub.2                                       184                                                                              "                CH.sub.2 CHCHCl                                           185                                                                              C.sub.2 H.sub.5  C.sub.2 H.sub.5                                           186                                                                              CH.sub.2 CHCH.sub.2                                                                            CH.sub.2 CHCH.sub.2                                       187                                                                              "                CH.sub.2 CH.sub.2 CN                                      188                                                                              CH.sub.2 CHCHCl  "                                                         189                                                                              "                CH.sub.2 CH.sub.2 OCOCH.sub. 3                            190                                                                              CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                  "                                                         191                                                                              CH.sub.2 CH.sub.2 COOCH.sub.3                                                                  CH.sub.2 CH.sub.2CH.sub.2                                 192                                                                               ##STR19##       H                                                           193                                                                             ##STR20##       "                                                           194                                                                            CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                                           "                                                         195                                                                              CH.sub.2 CH.sub.2 COOCH.sub.2 CHCH.sub.2                                                       "                                                         196                                                                              CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                  "                                                         197                                                                              CH.sub.2 CH.sub.2 CN                                                                           "                                                         198                                                                              CH.sub.2 CHOHCH.sub.2 Cl                                                                       "                                                         199                                                                              CH.sub.3         "                                                         200                                                                              H                "                                                         __________________________________________________________________________

The dyestuffs of the following Table 3 are also made in analogous mannerto the procedure of Examples 1 and 101. They correspond to the formula##STR21## and dye polyester in blue shades.

                                      TABLE 3                                     __________________________________________________________________________    Ex.                                                                           No. R.sub.1         R.sub.6  R.sub.5  R.sub.7    R.sub.8                      __________________________________________________________________________    201 COO(CH.sub.2).sub.5 CH.sub.3                                                                  H        CH.sub.3 C.sub.2 H.sub.5                                                                          CH.sub.2 CHOHCH.sub.3        202 COO(CH.sub.2).sub.7 CH.sub.3                                                                  H        "        "          CH.sub.2 CH.sub.2 OH         203 COOCH.sub.2 CH.sub.2 Cl                                                                       H        "        "          CH.sub.2 CH.sub.2                                                             COOC.sub.2 H.sub.5           204 COOCH.sub.2 CCH H        "        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.3            205 COOCH(CH.sub.2 OH)CH.sub.2Cl                                                                  H        "        "          "                            206 COOCH.sub.2 CHCH.sub.2                                                                        H        "        "          "                            207 COOCH.sub.2 CHCHCH.sub.3                                                                      H        "        C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5              208 COOCH(CH.sub.2 OCOCH.sub.3)CH.sub.3                                                           H        "        "          "                            209 COO(CH.sub.2 ).sub.3 CHCH.sub.2                                                               H        "        "          "                            210 COO(CH.sub.2).sub.2 CHCH.sub.2                                                                H        "        "          "                            211 COO(CH.sub.2).sub.2 CH(CH.sub.3).sub.2                                                        H        "        "          "                            212 COOCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                                                     H        "        "          "                            213 COOCH.sub.2 C.sub.6 H.sub.5                                                                   H        "        "          "                            214 COOCH.sub.2 CHOHCH.sub.3                                                                      H        "        "          "                            215 COOCH.sub.2 CBrCH.sub.2                                                                       H        "        "          "                            216 COOCH.sub.2 CH.sub.2 CH.sub.2 Br                                                              H        "        "          "                            217 COOCH.sub.2 CHCHBr                                                                            H        "        "          "                            218 COOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H        "        "          "                            219 COOC(CH.sub.3).sub.3                                                                          H        "        "          "                            220 COOCH.sub.2 CN  H        "        "          "                            221 COOC.sub.2 H.sub.5                                                                            H        "        CH.sub.2 CH.sub.2 ClCH.sub.3                                                             CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.3            222 COOCH.sub.3     H        "        C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCOO(CH.s                                                     ub.2).sub.9 CH.sub.3         223 COOC.sub.2 H.sub.4 COOC.sub.2 H.sub.5                                                         H        "        "          C.sub.2 H.sub.5              224 COOCH(CH.sub.3)CH.sub.2 OCOCH.sub.3                                                           H        "        "          "                            225 COOCH(C.sub.2 H.sub.5)CH.sub.2 OH                                                             H        "        "          "                            226 COOCH.sub.2 CHBrCl                                                                            H        "        "          "                            227 COOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                              H        "        "          "                            228 COOCH.sub.2 C(CH.sub.3).sub.3                                                                 H        "        "          "                            229 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                         H        "        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CH.sub.2                                                             CH.sub.2 CH.sub.3            230 COOCH.sub.3     H        "        "          "                            231 CONH.sub.2      H        "        "          "                            232 CONHC.sub.6 H.sub.5                                                                           H        "        CH.sub.2 CH.sub.2 OH                                                                     "                            233 COOCH.sub.2 C.sub.6 H.sub.4Cl(p)                                                              OC.sub.2 H.sub.5                                                                       NHCOCH.sub.3                                                                           H          H                            234 COO(CH.sub.2).sub.9 CH.sub.3                                                                  "        "        H          H                            235 COOC.sub.6 H.sub.11                                                                           OC.sub.2 H.sub.4 OCH.sub.3                                                             NHCOC.sub.2 H.sub.4 Cl                                                                 H          H                            236 CN              H        CH.sub.3 C.sub.2 H.sub.5                                                                          (CH.sub.2).sub.7                                                              CH.sub.3                     237 "               H        "        "          C.sub.2 H.sub.4 OCOOC.sub                                                     .2 H.sub.4 OC.sub.2                                                           H.sub.5                      238 COC.sub.6 H.sub.4 NO.sub.2 (p)                                                                H        "        C.sub.2 H.sub.4 OCOCH.sub.3                                                              C.sub.2 H.sub.4 OCOCH.sub                                                     .3                           239 COC.sub.6 H.sub.5                                                                             H        "        C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5 OCHO         240 COCH.sub.3      H        "        (CH.sub.2).sub.5 CH.sub.3                                                                (CH.sub.2).sub.5                                                              CH.sub.3                     241 CSNH.sub.2      H        "        C.sub.2 H.sub.5                                                                          "                            242 SO.sub.2 CH.sub.3                                                                             H        "        CH.sub.2 CH.sub.2 COOC.sub.2                                                  H.sub.5    CH.sub.2 C(CH.sub.3)CH.su                                                     b.2                          243 SO.sub.2C.sub.6 H.sub.5                                                                       H        "        C.sub.2 H.sub.4 OCOCH.sub.3                                                              C.sub.2 H.sub.4 OCOCH.sub                                                     .3                           244 SO.sub.2 C.sub.6 H.sub.4 CH.sub.3 (p)                                                         H        "        C.sub.2 H.sub.4 CN                                                                       "                            245 C.sub.6 H.sub.4NO.sub.2 (p)                                                                   H        "        C.sub.2 H.sub.5                                                                          CH.sub.2 CH.sub.2                                                             OCH.sub.2 CHCH.sub.2         246 "               H        NHCOCH.sub.3                                                                           "          CH.sub.2 CHOHCH.sub.3        247 benzimidazolyl(2)-                                                                            H        CH.sub.3 "          C.sub.2 H.sub.5              248 COO(CH.sub.2).sub.3 CH.sub.3                                                                  H        "        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                           CH.sub.2                                249                                                                                ##STR22##                                                                  250                                                                              ##STR23##                                                                __________________________________________________________________________

EXAMPLE 251

Proceeding as described in Example 1 and reacting the diazonium saltsolution described therein with a mixture of 22.1 partsN-ethyl-N-acetoxyethyl-m-toluidine, 5 parts urea, 100 parts glacialacetic acid and 200 parts ice, the dyestuff of to formula (c) ##STR24##which dyes polyesters and cellulose acetate in brilliant violet shades,is obtained.

9.9 Parts of the dyestuff of formula (c) are suspended in 50 partsnitromethane at 10°, 1 part 10% sodium methoxide solution is stirred inand the reaction mixture is stirred further at 10° for 3 hours. 25 partsacetic acid anhydride are added and the whole is heated to 100° in 10minutes. Stirring is effected at 100° for 30 minutes, the whole isallowed to cool and the precipitated dyestuff of formula (d) ##STR25##is filtered off. This dyestuff dyes polyester and cellulose acetate inbrilliant blue tones.

Further dyes which are made in analogy with the procedure of Examples 1and 251 are given in the following Table 4. They correspond to theformula ##STR26## In Examples 252 to 287 R is nitro, in Example 288--CH═CNNO₂ and in Example 289 --CH═C(C₂ H₅)--NO₂. The dyestuffs ofExamples 252 to 280 and 285 to 289 dye polyester fibres in blue shadesand those of Examples 281 to 284 in violet shades.

                                      TABLE 4                                     __________________________________________________________________________    Ex.                                                                           No.                                                                              R.sub.6                                                                            R.sub.5     R.sub.7        R.sub.8                                    __________________________________________________________________________    252                                                                              --OC.sub.2 H.sub.5                                                                 --NHCOCH.sub.3                                                                            --CH.sub.2 CH.sub.2 CN                                                                       --CH.sub.2 CH═CH.sub.2                 253                                                                              "    "           "              --CH.sub.2 CH═CH--Cl                   254                                                                              "    "           --CH.sub.2 CH.sub.2 COOCH.sub.3                                                              --CH.sub.2 C.tbd.CH                        255                                                                              "    "           --CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                                       --CH.sub.3                                 256                                                                              "    "           --CH.sub.2 CH.sub.2 CN                                                                       "                                          257                                                                              "    "           --C.sub.2 H.sub.4 OCOCH.sub.3                                                                --C.sub.2 H.sub.4 OCOCH.sub.3              258                                                                              --OCH.sub.3                                                                        "           --CH.sub.2 CH═CH--Cl                                                                     --CH.sub.2 CH═CHCl                     259                                                                              "    "           --CH.sub.2 CH═CH.sub.2                                                                   --CH.sub.2 CH═CH.sub.2                 260                                                                              "    "           --CH.sub.3     --CH.sub.3                                 261                                                                              H    "           --CH.sub.2 CH(CH.sub.3).sub.2                                                                --CH.sub.2 CH(CH.sub.3).sub.2              262                                                                              H    "           --C.sub.2 H.sub.5                                                                            --C.sub.2 H.sub.5                          263                                                                              H    "           --C.sub.2 H.sub.4 OCH.sub.3                                                                  --C.sub.2 H.sub.4 OCH.sub.3                264                                                                              H    --NHCOC.sub.2 H.sub.5                                                                     --C.sub.2 H.sub.5                                                                            --C.sub.2 H.sub.5                          265                                                                              H    --NHCOC.sub.2 H.sub.4 Cl                                                                  "              "                                          266                                                                              H    --NHCOOCH.sub.3                                                                           "              "                                          267                                                                              H    --NH--CHO   --C.sub.6 H.sub.13 (n)                                                                       --C.sub.6 H.sub.13 (n)                     268                                                                              --OC.sub.2 H.sub.5                                                                 --NHCOCH.sub.3                                                                            --C.sub.2 H.sub.4 COOCH.sub.2 CH═CHCl                                                    H                                          269                                                                              "    "           --C.sub.2 H.sub.4 COOCH.sub.2 CH.sub.2 OCH.sub.3                                             H                                          270                                                                              H    "           --C.sub.2 H.sub.4 COOCH.sub.2 CH(CH.sub.3).sub.2                                             H                                          271                                                                              H    --CH.sub.3  --C.sub.2 H.sub.5                                                                            --CH.sub.2 CHOHCH.sub.2 CH.sub.3           272                                                                              H    "           "              --C.sub.2 H.sub.4 OCOCH.sub.3              273                                                                              H    "           "              --C.sub.2 H.sub.4 OCH.sub.2 C.sub.6                                           H.sub.5                                    274                                                                              H    "           "              --C.sub.2 H.sub.4 OCH.sub.2 CH═CH--                                       Cl                                         275                                                                              H    "           --C.sub.4 H.sub.9 (n)                                                                        --C.sub.4 H.sub.9 (n)                      276                                                                              H    "           --CH.sub.2 CH(CH.sub.3).sub.2                                                                --CH.sub.2 CH(CH.sub.3).sub.2              277                                                                              H    "           --C.sub.2 H.sub.5                                                                            --CH.sub.2 C(CH.sub.3)═CH.sub.2        278                                                                              H    "           "              --CH.sub.2 --C.sub.6 H.sub.5               279                                                                              --OCH.sub.3                                                                        "           --CH.sub.3     --CH.sub.2 CH═CH--CH.sub.3             280                                                                              "    "           --CH.sub.2 CH═CH.sub.2                                                                   --CH.sub.2 CH═CH.sub.2                 281                                                                              "    "           --C.sub.2 H.sub.4 COOCH.sub.2 CH═CH--Cl                                                  H                                          282                                                                              "    "           --C.sub.2 H.sub.4 COO(CH.sub.3).sub.3 CH.sub.3                                               H                                          283                                                                              H    H           --C.sub.6 H.sub.5                                                                            H                                          284                                                                              H    H           --C.sub.2 H.sub.4 CN                                                                         --C.sub.2 H.sub.4 C.sub.6 H.sub.5          285                                                                              --OC.sub.2 H.sub.5                                                                 --NHCOCH.sub.3                                                                            --CH(CH.sub.3)--CH.sub.2 COOC.sub.2 H.sub.5                                                  H                                          286                                                                              --OC.sub.2 H.sub.5                                                                 --NHCOCH.sub.3                                                                            --C.sub.2 H.sub.4 COOCH.sub.3                                                                H                                          287                                                                              "    --NHCOOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                   --CH.sub.3     H                                          288                                                                              "    --NHCOCH.sub.3                                                                            --CH.sub.2 CH═CH.sub.2                                                                   --CH.sub.2 CH═CH.sub.2                 289                                                                              "    "           --C.sub.2 H.sub.4 CN                                                                         "                                          __________________________________________________________________________

The dyestuffs of the following Table 5 are prepared in analogy to theprocedure of Examples 1, 101 and 251. They correspond to the formula##STR27## and dye polyester fibres in blue tones.

                                      TABLE 5                                     __________________________________________________________________________    Ex.                                                                           No.                                                                              R                  R.sub.5                                                                              R.sub.6   R.sub.7         R.sub.8                __________________________________________________________________________    290                                                                              --CHO              --NHCOCH.sub.3                                                                       --OCH.sub.3                                                                             --CH(CH.sub.3 C.sub.4 H.sub.9                                                                 Hn)                    291                                                                              --CH═C(CN)COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                              "      --OC.sub.2 H.sub.5                                                                      --CH(CH.sub.3)C.sub.6 H.sub.11                                                                H                      292                                                                              --CHO              "      "         --CH(CH.sub.3)CH.sub.2 OCH.sub.2                                              CH.sub.2 OCH.sub.3                                                                            H                      293                                                                              --CH═C(CN)COOCH.sub.2 C(CH.sub.3)═CH.sub.2                                               "      --OCH.sub.2 CH.sub.2 OCH.sub.3                                                          --CH.sub.2 CH.sub.2 COOC.sub.2                                                H.sub.5         H                      294                                                                              --CH═CH--CO--C.sub.6 H.sub.4 NO.sub.2 (para)                                                 "      --OC.sub.2 H.sub.5                                                                      "               H                      295                                                                              --CH═CHCN      "      "         --CH.sub.2 CH═CH.sub.2                                                                    --CH.sub.2                                                                    CH═CH.sub.2        296                                                                              --CH═CHCHO     "      "         --CH.sub.2 CH.sub.2 CN                                                                        "                      297                                                                              --CH═CH--CH═C(CN)COOC.sub.2 H.sub.5                                                      --CH.sub.3                                                                           "         --C.sub.2 H.sub.                                                                              --C.sub.2 H.sub.5      298                                                                              --CH═CH--C.sub.6 H.sub.5                                                                     "      --OCH.sub.3                                                                             "               --CH.sub.2                                                                    CH.sub.2 CN            299                                                                              --CH═CH--C.sub.6 H.sub.4 NO.sub.2 (para)                                                     "      "         "               --CH.sub.2                                                                    CH.sub.2 OCOCH.sub.                                                           3                      __________________________________________________________________________

EXAMPLE 300

12.2 Parts 2-amino-4-chloro-5-formylthiazole are stirred in 50 partsglacial acetic acid and 25 parts 85% formic acid and cooled to 0°. At 0°to 5°, 5 parts pulverised sodium nitrite are shaken in portionwise overa period of 30 minutes and the whole is stirred for a further hour at 0°to 5°.

12.5 Parts 1-phenyl-3-methyl-5-aminopyrazole are dissolved in 50 partsglacial acetic acid and added to the above-mentioned suspension of2-nitrosamine-4-chlorothiazole-5-aldehyde. Stirring is effected at roomtemperature until no nitrosamine compound is detectable by thin layerchromatography. After cooling the dyestuff is precipitated with water,filtered and dried. The dyestuff, which dyes polyester, cellulosetriacetate and perlon in clear scarlet shades with good wet-, light- andsublimation-fastness, is of formula ##STR28##

Further dyes having the same good light and sublimation fastnesses areobtained by replacing 1-phenyl-3-methyl-5-aminopyrazole with thecompounds given in Table 6.

                  TABLE 6                                                         ______________________________________                                                                        Shade on                                      Ex.                             polyester                                     No.  compound                   fibres                                        ______________________________________                                        301  1-phenyl-3-methylpyrazolone-5                                                                            red                                           302  3-methylpyrazolone-5       "                                             303  1-(β-hydroxyethyl)-3-methylpyrazolone-5                                                             "                                             304  1-n-butyl-3-cyano-4-methyl-6-hydroxypyridone-2                                                           "                                             305  1-methyl-2-phenylindole    "                                             306  2-hydroxydiphenyl          "                                             307  p-cresol                   "                                             308  2-hydroxynaphthalene-3-carboxylic acid                                                                   "                                                  ethyl ester                                                              309  N--benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydro-                                                            violet                                             quinoline                                                                310  N--methyl-2,2,4-trimethyl-1,2,3,4-tetrahydro-                                                            "                                                  quinoline                                                                311  N--acetoxyethyl-2,2,4-trimethyl-1,2,3,4-tetra-                                                           "                                                  hydroquinoline                                                           312  2-diethylamino-4-phenyl-1,3-thiazole                                                                     violet                                        313  2-benzylamino-3-cyano-4-methyl-6-(β                                                                 red                                                hydroxyethyl)-pyridine                                                   314  N--ethoxyethyl-2,2,4-trimethyl-1,2,3,4-tetra-                                                            violet                                             hydroquinoline                                                           315  2,6-di(n-butylamino)-3-cyano-4-methylpyridine                                                            red                                           316  2,6-di-(3'-methoxypropylamino)-3-cyano-4-                                                                "                                                  methylpyridine                                                           317  N--(3'-methoxypropylamino)-4-                                                                            violet                                             hydroxy-naphthalimide                                                    318  2-benzylamino-3-cyano-4,6- red                                                bis-methylaminopyridine                                                  319  2,4,6-tris(3'-methoxypropylamino)-3-                                                                     "                                                  cyanopyridine                                                            320  1-N--cyanoethyl-naphthylamine                                                                            blue                                          ______________________________________                                    

APPLICATION EXAMPLE

7 Parts of the dye of Example 1 are ground to a fine powder with 4 partssodium dinaphthylmethanedisulphonic acid, 4 parts sodium cetyl sulphateand 5 parts anhydrous sodium sulphate in a ball mill for 48 hours.

1 Part of the so obtained dyestuff preparation is pasted with a littlewater and the suspension is added through a sieve to a dyebathcontaining 4000 parts water and 3 parts sodium laurylsulphate. Theliquor ratio is 1:40. 100 parts polyester fibres are added at 40° to 50°and 20 parts chlorinated benzene emulsified in water are added thereto.The bath is slowly heated to 100° and dyeing is effected for 1 to 2hours at 95° to 100°. The blue-dyed fibres are washed, soaped, washedagain and dried. The dyeing is level and has good fastnesses to light,overdyeing, washing, water, sea-water, sweat, sublimation, fumesthermofixation, pleating and permanent pressing.

What is claimed is:
 1. A compound of the formula ##STR29## wherein K isthe radical of a coupling component, said coupling component being1-phenyl-3-methyl-5-aminopyrazole,1-phenyl-3-methylpyrazolone-5,3-methylpyrazolone-5,1-(2'-hydroxyethyl)-3-methylpyrazolone-5,1-n-butyl-3-cyano-4-methyl-6-hydroxypyridone-2,1-methyl-2-phenylindole,2-hydroxydiphenyl, p-cresol, 2-hydroxynaphthalene-3-carboxylic acidethyl ester, 2-diethylamino-b 4-phenyl-1,3-thiazole,2-benzylamino-3-cyano-4-methyl-6-(2'-hydroxyethyl)pyridine,2,6-di-(n-butylamino)-3-cyano-4-methylpyridine,2,6-di(3'-methoxypropylamino)-3-cyano-4-methylpyridine,2-benzylamino-3-cyano-4,6-di-(methylamino)pyridine,2,4,6-tri-(3'-methoxypropylamino)-3-cyanopyridine,1-(N-cyanoethyl)naphthylamine orN-(3'-methoxypropylamino)-4-hydroxynaphthalimide, ##STR30## wherein R₅is hydrogen; C₁₋₂ alkyl; C₁₋₂ alkoxy; cyano; formamido; (C₁₋₄alkyl)carbonylamino; (C₁₋₄ alkyl)carbonylamino the alkyl moiety of whichis monosubstituted by hydroxy, chloro, bromo, C₁₋₄ alkoxy, phenyl,phenoxy, benzloxy or (C₁₋₂ alkoxy)carbonyl; benzamido; acryloylamino;allylcarbonylamino; aminocarbonylamino; (C₁₋₄ alkyl)aminocarbonylamino;(C₁₋₄ alkoxy)carbonylamino; (C₁₋₄ alkoxy)carbonylamino the alkoxy moietyof which is monosubstituted by C₁₋₂ alkoxy or phenyl; C₁₋₂alkylsulfonylamino; phenylsulfonylamino; di-(C₁₋₂alkyl)aminosulfonylamino; chloro or bromo,R₆ is hydrogen, chloro, bromo,C₁₋₂ alkyl, C₁₋₂ alkoxy or (C₁₋₂ alkoxy)ethoxy, with the proviso thatnot more than one of R₅ and R₆ is chloro or bromo, R₇ is hydrogen; C₁₋₈alkyl; C₁₋₄ alkyl substituted by 1 or 2 substituents each of which isindependently chloro, bromo, hydroxy, thiocyano, cyano, (C₁₋₄alkyl)carbonyl, (C₁₋₄ alkoxy)carbonyl, formyloxy, (C₁₋₁₀alkyl)carbonyloxy, cyclohexyl, (C₁₋₃ chloroalkyl)carbonyloxy, (C₁₋₃bromoalkyl)carbonyloxy, (C₁₋₁₀ alkoxy)carbonyloxy, (C₁₋₂alkoxy)ethoxycarbonyloxy, (C₃₋₄ alkenyl)oxycarbonyl,chloroallyloxycarbonyl, bromoallyloxycarbonyl, C₃₋₄ alkenyloxy,chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C₁₋₄ alkoxy,phenyl, phenoxy or phenyl(C₁₋₄ alkoxy), with the proviso that not morethan one substituent is a member of the group consisting of benzoyloxy,phenyl, phenoxy and and phenyl(C₁₋₄ alkoxy); (C₁₋₄ alkoxy)C₁₋₄ alkyl thealkoxy moiety of which is monosubstituted by chloro, bromo, cyano, C₁₋₄alkoxy, (C₁₋₄ alkoxy)carbonyl, (C₁₋₄ alkoxy)carbonyloxy or (C₁₋₄alkyl)carbonyloxy; C₃₋₄ alkenyl; C₃₋₄ alkenyl monosubstituted by phenyl,chloro or bromo; propynyl; C₅₋₇ cycloalkyl; cyclohexyl substituted by 1,2 or 3 methyl groups; phenyl or phenyl substituted by 1, 2 or 3substituents each of which is independently chloro, bromo, methyl orC₁₋₂ alkoxy, R₈ is hydrogen; C₁₋₈ alkyl; C₁₋₄ alkyl monosubstituted bychloro, bromo, hydroxy, cyano, thiocyano, (C₁₋₄ alkyl)carbonyl, (C₁₋₄alkoxy)carbonyl, formyloxy, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄chloroalkyl)carbonyloxy, (C₁₋₄ bromoalkyl)carbonyloxy, (C₁₋₄alkoxy)carbonyloxy, (C₁₋₂ alkoxy)ethoxycarbonyloxy, (C₃₋₄alkenyl)oxycarbonyl, chloroallyloxycarbonyl, bromoallyloxycarbonyl, C₃₋₄alkenyloxy, chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C₁₋₄alkoxy, phenyl, phenoxy, phenyl(C₁₋₄ alkoxy), carbamoyl, (C₁₋₄alkyl)carbamoyl, di-(C₁₋₄ alkyl)carbamoyl, (C₁₋₄ alkyl)carbamoyloxy,di-(C₁₋₄ alkyl)carbamoyloxy, phenylcarbamoyl, phenylcarbamoyloxy,phthalimidyl-2, succinimidyl-2, saccharinyl-2, pyridyl orbenzothiazolyl-2-mercapto; (C₁₋₄ alkoxy)C₁₋₄ alkyl the alkoxy moiety ofwhich is monosubstituted by chloro, bromo, cyano, C₁₋₄ alkoxy, (C₁₋₄alkoxy)carbonyl, (C₁₋₄ alkoxy)carbonyloxy or (C₁₋₄ alkyl)carbonyloxy;2-hydroxy, (C₁₋₄ alkyl)carbonyloxy or (C₃₋₄alkenyl)carbonyloxy-3-allyloxypropyl; 2-hydroxy, (C₁₋₄ alkyl)carbonyloxyor (C₃₋₄ alkenyl)carbonyloxy-3-propynyloxypropyl; C₃₋₄ alkenyl or C₃₋₄alkenyl monosubstituted by chloro, bromo or phenyl, or R₇ and R₈ takentogether and with the nitrogen atom to which they are joined arepiperidino or morpholino, R_(x) is hydroxyethyl, methyl, ethyl,methoxycarbonylethyl, ethoxycarbonylethyl, benzyl, methoxyethyl,ethoxyethyl or acetoxyethyl,and R_(y) is hydrogen, methyl or acetamido,R is --CHO, --CH═C(CN)--R₁, --CH═CH--R₂, --CH═C(NO₂)--R₃, --CH═NOH or--CN,wherein R₁ is (C₁₋₁₀ alkoxy)carbonyl; (C₁₋₁₀ alkoxy)carbonylmonosubstituted by chloro, bromo, cyano, hydroxy, C₁₋₂ alkoxy, (C₁₋₂alkyl)carbonyloxy or (C₁₋₂ alkoxy)carbonyl; (C₁₋₁₀ alkoxy)carbonyldisubstituted by hydroxy and by chloro or bromo; (C₃₋₈alkenyl)oxycarbonyl; (C₃₋₈ chloroalkenyl)oxycarbonyl; (C₃₋₈bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl;chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C₁₋₄ alkylsulfonyl;phenylsulfonyl; tolylsulfonyl; carbamoyl; (C₁₋₂ alkyl)carbamoyl;di-(C₁₋₂ alkyl)carbamoyl; phenylcarbamoyl; aminothiocarbonyl;benzimidazolyl-2; cyano; acetyl; phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro groups is two, and R₂ is phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro groups is two, and R₃ is hydrogen, methyl or ethyl, and m is 0 or1,with the provisos that (i) when R is --CN, m must be 1, and (ii) themolecule is free of ##STR31## radicals.
 2. A compound according to claim1 having the formula ##STR32## wherein K is ##STR33## wherein R₅ ishydrogen; C₁₋₂ alkyl; C₁₋₂ alkoxy; cyano; formamido; (C₁₋₄alkyl)carbonylamino; (C₁₋₄ alkyl)carbonylamino the alkyl moiety of whichis monosubstituted by hydroxy, chloro, bromo, C₁₋₄ alkoxy, phenyl,phenoxy, benzyloxy or (C₁₋₂ alkoxy)carbonyl; benzamido; acryloylamino;allylcarbonylamino; aminocarbonylamino; (C₁₋₄ alkyl)aminocarbonylamino;(C₁₋₄ alkoxy)carbonylamino; (C₁₋₄ alkoxy)carbonylamino the alkoxy moietyof which is monosubstituted by C₁₋₂ alkoxy or phenyl; C₁₋₂alkylsulfonylamino; phenylsulfonylamino; di-(C₁₋₂alkyl)aminosulfonylamino; chloro or bromo,R₆ is hydrogen, chloro, bromo,C₁₋₂ alkyl, C₁₋₂ alkoxy or (C₁₋₂ alkoxy)ethoxy, with the proviso thatnot more than one of R₅ and R₆ is chloro or bromo, R₇ is hydrogen; C₁₋₈alkyl; C₁₋₄ alkyl substituted by 1 or 2 substituents each of which isindependently chloro, bromo, hydroxy, thiocyano, cyano, (C₁₋₄alkyl)carbonyl, (C₁₋₄ alkoxy)carbonyl, formyloxy, (C₁₋₁₀alkyl)carbonyloxy, cyclohexyl, (C₁₋₃ chloroalkyl)carbonyloxy, (C₁₋₃bromoalkyl)carbonyloxy, (C₁₋₁₀ alkoxy)carbonyloxy, (C₁₋₂alkoxy)ethoxycarbonyloxy, (C₃₋₄ alkenyl)oxycarbonyl,chloroallyloxycarbonyl, bromoallyloxycarbonyl, C₃₋₄ alkenyloxy,chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C₁₋₄ alkoxy,phenyl, phenoxy or phenyl(C₁₋₄ alkoxy), with the proviso that not morethan one substituent is a member of the group consisting of benzoyloxy,phenyl, phenoxy and and phenyl(C₁₋₄ alkoxy); (C₁₋₄ alkoxy)C₁₋₄ alkyl thealkoxy moiety of which is monosubstituted by chloro, bromo, cyano, C₁₋₄alkoxy, (C₁₋₄ alkoxy)carbonyl, (C₁₋₄ alkoxy)carbonyloxy or (C₁₋₄alkyl)carbonyloxy; C₃₋₄ alkenyl; C₃₋₄ alkenyl monosubstituted by phenyl,chloro or bromo; propynyl; C₅₋₇ cycloalkyl; cyclohexyl substituted by 1,2 or 3 methyl groups; phenyl or phenyl substituted by 1, 2 or 3substituents each of which is independently chloro, bromo, methyl orC₁₋₂ alkoxy, R₈ is hydrogen; C₁₋₈ alkyl; C₁₋₄ alkyl monosubstituted bychloro, bromo, hydroxy, cyano, thiocyano, (C₁₋₄ alkyl)carbonyl, (C₁₋₄alkoxy)carbonyl, formyloxy, (C₁₋₄ alkyl)carbonyloxy, (C₁₋₄chloroalkyl)carbonyloxy, (C₁₋₄ bromoalkyl)carbonyloxy, (C₁₋₄alkoxy)carbonyloxy, (C₁₋₂ alkoxy)ethoxycarbonyloxy, (C₃₋₄alkenyl)oxycarbonyl, chloroallyloxycarbonyl, bromoallyloxycarbonyl, C₃₋₄alkenyloxy, chloroallyloxy, bromoallyloxy, propynyloxy, benzoyloxy, C₁₋₄alkoxy, phenyl, phenoxy, phenyl(C₁₋₄ alkoxy), carbamoyl, (C₁₋₄alkyl)carbamoyl, di-(C₁₋₄ alkyl)carbamoyl, (C₁₋₄ alkyl)carbamoyloxy,di-(C₁₋₄ alkyl)carbamoyloxy, phenylcarbamoyl, phenylcarbamoyloxy,phthalimidyl-2, succinimidyl-2, saccharinyl-2, pyridyl orbenzothiazolyl-2-mercapto; (C₁₋₄ alkoxy)C₁₋₄ alkyl the alkoxy moiety ofwhich is monosubstituted by chloro, bromo, cyano, C₁₋₄ alkoxy, (C₁₋₄alkoxy)carbonyl, (C₁₋₄ alkoxy)carbonyloxy or (C₁₋₄ alkyl)carbonyloxy;2-hydroxy, (C₁₋₄ alkyl)carbonyloxy or (C₃₋₄alkenyl)carbonyloxy-3-allyloxypropyl; 2-hydroxy, (C₁₋₄ alkyl)carbonyloxyor (C₃₋₄ alkenyl)carbonyloxy-3-propynyloxypropyl; C₃₋₄ alkenyl or C₃₋₄alkenyl monosubstituted by chloro, bromo or phenyl, or R₇ and R₈ takentogether and with the nitrogen atom to which they are joined arepiperidino or morpholino, R_(x) is hydroxyethyl, methyl, ethyl,methoxycarbonylethyl, ethoxycarbonylethyl, benzyl, methoxyethyl,ethoxyethyl or acetoxyethyl,and R_(y) is hydrogen, methyl or acetamido,R is --CHO, --CH═C(CN)--R₁, --CH═C--R₂, --CH═C(NO₂)--R₃, --CH═NOH or--CN,wherein R₁ is (C₁₋₁₀ alkoxy)carbonyl; (C₁₋₁₀ alkoxy)carbonylmonosubstituted by chloro, bromo, cyano, hydroxy, C₁₋₂ alkoxy, (C₁₋₂alkyl)carbonyloxy or (C₁₋₂ alkoxy)carbonyl; (C₁₋₁₀ alkoxy)carbonyldisubstituted by hydroxy and by chloro or bromo; (C₃₋₈alkenyl)oxycarbonyl; (C₃₋₈ chloroalkenyl)oxycarbonyl; (C₃₋₈bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl;chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C₁₋₄ alkylsulfonyl;phenylsulfonyl; tolylsulfonyl; carbamoyl; (C₁₋₂ alkyl)carbamoyl;di-(C₁₋₂ alkyl)carbamoyl; phenylcarbamoyl; aminothiocarbonyl;benzimidazolyl-2; cyano; acetyl; phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro groups is two, and R₂ is phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro groups is two, and R₃ is hydrogen, methyl or ethyl, and m is 0 or1,with the provisos that (i) when R is --CN, m must be 1, and (ii) themolecule is free of ##STR34## radicals.
 3. A compound according to claim2 wherein R is --CHO, --CH═C(CN)--R₁, --C═CH--R₂, --CH═C(NO₂)--R₃ or--CH═NOH.
 4. A compound according to claim 3 wherein m is
 0. 5. Acompound according to claim 4 wherein R is --CHO.
 6. A compoundaccording to claim 3 wherein R is --CHO, --CH═C(CN)--R₁ or--CH═C(NO₂)--R₃.
 7. A compound according to claim 3 whereinR₁ is (C₃₋₆alkoxy)carbonyl or (C₃₋₆ alkenyl)oxycarbonyl,and R₃ is hydrogen.
 8. Acompound according to claim 7 whereinR is --CHO, --CH═C(CN)--R₁ ' or--CH═CH--NO₂,wherein R₁ ' is (C₃₋₆ alkoxy)carbonyl or (C₃₋₆alkenyl)oxycarbonyl.
 9. A compound according to claim 8 whereinR is--CHO or --CH═C(CN)--R₁ ', wherein R₁ ' is (C₃₋₆ alkoxy)carbonyl or(C₃₋₆ alkenyl)oxycarbonyl.
 10. A compound according to claim 7 whereinKis ##STR35## wherein R₅ ' is hydrogen, methyl or --NH--CO--R₉, whereinR₉ is hydrogen, C₁₋₄ alkoxy, (C₁₋₂ alkoxy)ethoxy, C₁₋₂ alkyl or C₁₋₂alkyl monosubstituted by chloro, bromo or C₁₋₂ alkoxy, R₆ ' is hydrogen,methyl, methoxy, ethoxy or (C₁₋₂ alkoxy)ethoxy, R₇ ' is hydrogen; C₃₋₄alkenyl; C₁₋₆ alkyl; C₂₋₃ alkyl monosubstituted by hydroxy, allyloxy,propynyloxy, cyano, (C₁₋₄ alkoxy)carbonyl or (C₃₋₄ alkenyl)oxycarbonylor C₂₋₃ alkyl substituted by 1 or 2 substituents each of which isindependently C₁₋₃ alkoxy, (C₁₋₃ alkyl)carbonyloxy or (C₁₋₃alkoxy)carbonyloxy,and R₈ ' is C₁₋₄ alkyl, benzyl, phenylethyl or C₂₋₃alkyl monosubstituted by hydroxy, C₁₋₃ alkoxy, allyloxy, propynyloxy,cyano, (C₁₋₃ alkyl)carbonyloxy, (C₁₋₄ alkoxy)carbonyl, (C₃₋₄alkenyl)oxycarbonyl, (C₁₋₃ alkoxy)carbonyloxy or phenoxy.
 11. A compoundaccording to claim 10 whereinR₅ ' is hydrogen or methyl, and R₆ ' ishydrogen.
 12. A compound according to claim 11 whereinR₇ ' is ethyl, andR₈ ' is ethyl.
 13. A compound according to claim 3 wherein K is##STR36##
 14. A compound according to claim 13 wherein m is
 0. 15. Acompound according to claim 13 wherein R is --CHO, --CH═C(CN)--R₁ or--CH═C(NO₂)--R₃.
 16. A compound according to claim 15 wherein m is 0.17. A disperse dye of the formula ##STR37## wherein K is the radical ofa coupling component of the aniline, α-naphthylamine, pyrazlone,aminopyrazole, indole, tetrahydroquinoline, thiazole, phenol, napthol,pyridine or pyridone series,R is --CHO, --CH═C(CN)--R₁, --CH═CH--R₂,--CH═C(NO₂)--R₃, --CH═NOH or --CN, wherein R₁ is (C₁₋₁₀ alkoxy)carbonyl;(C₁₋₁₀ alkoxy)carbonyl monosubstituted by chloro, bromo, cyano, hydroxy,C₁₋₂ alkoxy, (C₁₋₂ alkyl)carbonyloxy or (C₁₋₂ alkoxy)carbonyl; (C₁₋₁₀alkoxy)carbonyl disubstituted by hydroxy and by chloro or bromo; (C₃₋₈alkenyl)oxycarbonyl; (C₃₋₈ chloroalkenyl)oxycarbonyl; (C₃₋₈bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl;chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C₁₋₄ alkylsulfonyl;phenylsulfonyl; tolylsulfonyl; carbamoyl; (C₁₋₂ alkyl)carbamoyl;di-(C₁₋₂ alkyl)carbamoyl; phenylcarbamoyl; aminothiocarbonyl;benzimidazolyl-2; cyano; acetyl; phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro grups is two, and R₂ is phenyl; benzoyl or phenyl or benzoylsubstituted by 1, 2 or 3 substituents each of which is independentlychloro, bromo or nitro, with the proviso that the maximum number ofnitro groups is two, and R₃ is hydrogen, methyl or ethyl, and m is 0 or1, with the provisos that (i) when R is --CN, m must be 1, and (ii) themolecule is free of ##STR38## radicals.